We like how they had to crudely draw a cigarette in his mouth that clearly wasn't there when he posed for the, uh, painting. "What is that, Chesterfield? I'm not putting that shit in my mouth. Just paint one in, Picasso."

Also, just think of how many more kids were able to follow First Lady Nancy Reagan's "Just Say No" campaign thanks to her husband kicking off children's literacy by introducing us to the ABC's of smooth Chesterfield cigarettes:

Via Tjsrecords.com"Kids, whenever you feel tempted by drugs, just smoke a whole carton of Chesterfields instead."

Did It Work?

Chesterfield's new home at Altria Group Inc., better known as the parent company previously known as Philip Morris Companies Inc., was able to spend more than $107 million on lobbying during the George W. Bush years alone, so they appear to be all right. It's all about making the right friends early.

#1. Bob Dole Advertises for Viagra, and Everything Else

The Man:

War hero. Former Senate Majority Leader. Referred to himself in the third person. He was Gerald Ford's running mate in the 1976 election, and the Republican nominee for president in 1996. Also, much like Gerald Ford, he had a tendency to fall down on camera.

"Who's the fucking corpse who built this shitty rail?!"

Dole was in his mid-70s when he got out of the politics game, so as a well-to-do, pro-business politician in retirement, he would have had all kinds of options. He could either go the classy route (advertising fine suits, or maybe a line of expensive scotch for the country club Republican market) or appeal to the seniors (advertise for the AARP, or that necklace that lets you call an ambulance when you break a hip).

There are lots of dignified options for a man of his stature, and he surely wasn't hurting for money (after leaving politics he worked in a high-end law firm and hit the lucrative public speaking circuit). The man could pick his opportunities.

In 1999, at the age of 75, he made what has to be one of the ballsiest endorsement decisions in the history of advertising. Bob Dole took to the cameras and essentially said, "I'm pushing 80, and I don't get the boners like I used to. But trust me, I still like to have naked boner sex with the ladies. Are you picturing me having sex now? No? How about now? Are you picturing my balls?"

Getty"Nice sign. Mind if I fuck it?"

Dole was a funny guy, always willing to make jokes at his own expense. So when he went on a run of advertisements all around that same time, it wasn't clear if he really needed the money (due to some gambling debts or something), or if he just wanted to stay in the public eye, or if he just thought it was hilarious.

Whatever the reason, Dole would start turning up in more ads than Michael Jordan, pitching Visa, Dunkin' Donuts and Pepsi-Cola in an advertising campaign that put his presidential campaign to shame.

Did It Work?

Yes and hell yes. Bob Dole's new career as a commercial spokesman not only put a rocket in addition to some extra money in his pocket, but he eventually got to share a Super Bowl commercial with Britney Spears in 2002 for Pepsi. Sure enough, the commercial included a not-so-subtle reference to how Bob Dole was now the proud owner of a medically induced, rock-hard penis.

Yeah, it's not a Nobel Prize, but at least it's something that both he and the Mrs. can be proud about.

Via Reason.com"Laugh all you want. I get more tail at 75 than you do now."

For more bizarre endorsements from famous figures, pick up a copy of Jacopo's book "Go @#$% Yourself!" -- An Ungentlemanly Disagreement, by Filippo Argenti, available in paperback and DRM-free on Kindle.

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